My Boyfriend is Wonderful, but Not Ambitious or Successful

My Boyfriend is Wonderful, but Not Ambitious or Successful

Hi Evan,

I have been struggling with the fact I have a wonderful man in my life who loves me more than I’ve ever felt loved, but I’m just not satisfied somehow. We have known one another for about ten years dating on and off, taking a four year break at one point. He is VERY persistent and continues to take me back into his life if I let him. We are compatible on many levels, but there is one thing that continues to turn me off (from ten years ago to now) and that is his lack of ambition to be successful professionally. I wouldn’t be picky about his career field of choice but at the rate it’s going I’ll never see him in a 6 o’clock loosened tie… which is a huge turn on for me.

I’m very much that young professional go getter with the high stress job, always moving to the next promotion. I’m busy all the time professionally and personally because I thrive on feeling accomplished. He on the other hand is satisfied with bringing home an okay pay check to put food on his table, not that concerned with finishing college (he’s 31) and rarely has anything interesting to talk about outside of “us”, movies, and other media outlet driven conversation. A full day of freedom in my life does not revolve around TV, 90% of his would.

I can’t let go of wishing he were a stronger, more creative, more successful man who I could look to for experienced life advice. I’m very independent but I’d also like to get some reassurance and empathy from a reliable source from time to time. I know that’s harsh. I would never say those things to him, but it’s how I feel. I find the sexiest thing about a man is his intelligence, and no matter if a person is well read or not, a great deal of intelligence comes from professional life experience. Please tell me I’m being too hard on him and myself.  I should be happy to have a man who loves me and I can trust.


Thank you, CJ, for writing one of the most self-aware letters I’ve run. I think everyone here can feel your pain. Love is only easy when we’re so whipped that we can’t even think clearly. In such circumstances, there are no decisions to be made. But right now, you’re seeing things quite clearly. Which means the world is grey, not black and white.

Love is only easy when we’re so whipped that we can’t even think clearly.

So before I get into talking about him, let’s talk about you.

You’re not a gold-digger for wanting a guy who is more ambitious.
You’re not snobby for finding intelligence sexy.
You’re not shallow for craving conversation that doesn’t revolve around pop culture.
And you’re not wrong for wishing he were stronger, more creative, and more experienced professionally.

The questions that linger for me are these….

1)    Are compatibility and kindness more important than worldliness and ambition?
2)    Is it realistic to think that you can find a worldly, professional man who is as kind and compatible as your current boyfriend?

This is the calculus of dating. And the same answers don’t apply to everyone. Which is why giving advice on such individual matters is somewhere between impossible and pointless.

But that doesn’t mean I can’t try.

Someone told me recently that women expect men to fulfill ALL of their needs, which sets them up for failure. They want men to fulfill the role of their best girlfriend and their rock solid Marlboro Man simultaneously. As I said in “Men Don’t Go Both Ways” chapter of “Why You’re Still Single”, these are different men and you’ll always be disappointed if you expect a man to cover all bases. Strangely, this is one area in which I think men “get it” more. We can compartmentalize. Which is why we’d rather watch football with only the guys, while you’d like us to come shoe shopping with you.

Point is, it’s a failing proposition to expect one man to be all things to you. Thus, you have to make hard choices. What’s most important to you? And what things can you NOT get from anyone BUT your boyfriend?

I’ve wrestled with that myself, because, like you, I get a rise out of ambition, philosophy, and creativity. Who doesn’t? But I can talk to my business coach about my business, I can talk to my best guy friend about philosophy, and I can experience my own creativity and others’ creativity in 1000 other forms. But I can’t make love to my business coach. I can’t wake up next to my best guy friend. And with all the art and culture out in the world, I don’t need my spouse to be a creator as much as an appreciator.

I get the joy of sophistication. It’s fun to feel like the witty, urbane couple that can break bread with the prime minister if need be. Just know that apart from the spark you feel around a sophisticate, it doesn’t have much inherent value. The ability to quote Proust pales in comparison with the person who will drive you to your chemo treatments in thirty years.

The ability to quote Proust pales in comparison with the person who will drive you to your chemo treatments in thirty years.

So, back to the original question: are compatibility and kindness more important than worldliness and ambition? Well, if it were either kindness OR worldliness, I’d say yes. But there are ambitious people who are kind as well. And it would be easy to tell you to dump your guy and seek one of these guys out. The thing is that most good qualities often come with bad qualities as well. The ambitious guy may work 70 hours a week. The sophisticated guy may be a know-it-all and a snob. You just don’t know until you put yourself out there. There’s a pretty big risk in doing so.

I would encourage you to look long and hard at what really matters, CJ, and how hard it is to find it. For years, I said that I wasn’t jealous of any of my married friends because it’s not like they married MY wife. And I meant it – I never really met anyone with whom I was super-compatible. But now that I have someone with whom I’m super-compatible, my mind succumbs to the temptation – what if there’s someone else? Someone younger. Someone more accomplished. Someone more well-read.

Is there someone like that out there? Maybe. But she wouldn’t have the number one quality that my girlfriend has: she accepts me as I am, and loves me unconditionally. No other girlfriend I’ve ever had has done that. Which is why I’m keeping her and never letting her go.

I can’t say what’s right for you, my friend. Intellectual stimulation matters. Money definitely matters. But if you can get stimulation from other people and you can make money yourself, why not land the one thing you can’t get anywhere else – a partner for life?

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  1. 121

    I would like to say that I as a guy do not dislike all women. given my negative views. I do like women. I don’t like want many many women DO.

    This is exactly how I feel about most men. I don’t dislike men at all. I love them. I love how they are different from me. But at the same time, sometimes those differences cause alot of pain and angst for me. I don’t like what many many men DO. Men don’t expect me to pay for dates or financially support them. But there are other things men do that hurt women just as much as men are hurt by women who don’t want to meet halfway for financial items. But whenever I attempt to have a dialogue with a man about these things, they are brushed aside, I am told I am silly or over emotional, or that “that’s just the way men are so deal with it”. I say this to point out to you Vino, and other male members that there are things women do that hurt you and there are things men do that hurt women. And I think both sides want some understanding on that score without being told they are evil or hate the opposite sex.

    I think the issue alot of men have with money and women, is the same issue I have with men and porn/strip clubs/checking out other women. For me, this is an equal comparison because it appears that there are similar feelings on how the opposite sex deals with these very difference issues.

    And Eda..good post!

  2. 122

    “…men communicate verbally with less nuance than women and therefore don’t understand why we’re hurt when they’re blunt and rude”

    I think it is important to distinguish between bluntness and directness on one hand, and rudeness and shock value on the other hand.

    Part of the difference between the sexes is in communication, not just biological differences. I think men are generally socialized to communicate directly and bluntly. Women, on the other hand like to ‘circle the airport’ as I prefer to call it.

    Often, it’s very easy and tempting to think someone who’s being direct is being rude, just because one dislikes the directness and uncomfortable content of what they say. Sometimes honesty does have shock value, just because it’s honest, not because it’s over-stated.

    I also think that directness actually makes men in general far better communicators than given credit for. (excuse poor sentence structure)

    I also think it’s part of the tension between the sexes – accepting people for how they are, and communicate, rather than demand that they do things the way I may want them to. I may find it endearing that my girlfriend can take 15 minutes to tell me what transpired with a friend in 3 minutes. I may not want to hear that every time, though. OTOH, she’d need to accept my ‘See Spot run’ way of communicating.

    Give & take….

  3. 123

    To vino,

    Check out this well known fact. 85% of communication is body language. LOL!….

  4. 124

    Then why, oh why, do women talk soooo much? 😉

  5. 125

    I also think that directness actually makes men in general far better communicators than given credit for. (excuse poor sentence structure)

    But don’t you see? This is where issues and arguments come into play. When one sex sees their way of doing things as the better way instead of understanding the differences. The truth is, that the way men and women communicate isn’t better or worse then the other. It’s different. The fact that men are more direct doesn’t mean men are better communicators. . The fact that women “cirlce the airport” to communicate what they are saying doesn’t mean women are better or worse communicators either. Both styles have their place. But when you write off women’s way of communicating, just as if a woman did the say to men, as being less, you are only adding to the problem. It’s important to not degrade the way the opposite sex does something just because it’s not the way you would do it.

  6. 126

    Ummm JG,

    I didn’t say men were better communicators. Nor did I ‘write off’ women’s manner of communicating. That is your assumption, the words you seek to put into my mouth. I said:

    “I also think that directness actually makes men in general far better communicators than given credit for.”

    Don’t wish to argue, but it does appear as though you haven’t actually LISTENED to what I said.

    Part of the problem, no?

  7. 127

    Michele (#16) said:
    “Your attraction to the 6 PM loose tie guy may/not alter over time, but I can assure you that a man in his early 30’s who is into the status quo is NOT going to change.”

    This is an unfair assumption to make, especially with the current generation in that age bracket. As you mentioned, you are a baby boomer, so you can be forgiven for not realizing that, for better or worse, many of our generation, male and female alike, have extended the period of adolescence.
    I dropped out of college at 23, and I am only now, at 32, getting my act together, after a decade-long decline in my fortunes. I’ve gone back to school, and I’m doing rather well. My success in the classes I am taking has boosted my confidence in other areas, so I’m also getting back into shape and reading more broadly.
    I’ve always been a literate, cultured, adventurous guy, but for too many years I was satisfied with a bare-bones bohemian existence. My last relationship (she was an engineer!) was disastrous, precisely because my own dissatisfaction with my life was eating away at my self-esteem, and frankly, turning me into a bitter, boring slob.

    But hey, like I said, things are looking up. It’s never to late to make something of yourself. I know one guy who became a successful computer programmer without ever having used a computer before the age of 40, and another who got his architect’s license at 50!

    I’ve been so busy that I haven’t dated much in this first year of the rest of my life, but those women I have dated have been pleasant, succesful, and apparently more interested in my current road to success (as well as my many interesting experiences) than the often crooked paths and dead-ends of my not-too-distant past, which I haven’t felt the need to hide.

  8. 128
    Don't want to say

    Wow. It was like I wrote this. Thank you so much for your answer. I have been crying over this for a long time. I now feel like I know how to think through this. God bless you!

  9. 129

    CJ’s problem, the orginal post concern, is EXACTLY the same as what I am going through. The replies at the start, and Evan’s answer, have made for amazing reading. Every post said something significant and valid, something for me to think about. However, I got a big confused as I read further on and felt that we began to stray a little off topic…
    But the advice, observations and theories offered have been very, very useful. It’s made me look at my relationship from all angles, I’m very glad I found this site, thank you.

  10. 130

    Thank you for this thoughtful and insightful post. You have helped me TREMENDOUSLY. My mother is convinced that me and my serious boyfriend are not compatible because we have different levels of ambition (I am very ambitious, he is not). I have felt that somehow it can’t be so black and white, and you have helped put words to what I know is true. He doesn’t have to be ambitious for our relationship to work. I would love for him to be a stay at home Dad, for example. I can talk about work “stuff” and my professional life with my [large enough!] network and professional friends. I absolutely don’t need him to fulfill every waking need and whim that courses through my body! Thank you, a million times thank you, for helping me to put my mother’s worries to rest. The case is closed, from where I stand!

  11. 131
    Caro Ferrero

    I have just ended my relationship. It had been 3 years and by boyfriend had not been able to keep a job for more than a month (because these are boring or not what he wants and expects for his ”professional career”), and in fact these jobs have not exceeded 4 or 5 jobs (hence 4 or 5 months).  He is very good at what he does (if he wants to work), yet talking to him about things outside his “comfort zone” make him terribly depressed (making it harder for him to decide to find a new job).
    In order for you to understand the full picture, I will describe a month of our relationship. I work all week, go to postgraduate classes twice a week, and run with my running team most “free” days; leaving me just Saturday and Sunday as the “relationship days” of the week.
    Because of current economy, i was forced to move back to my mother’s house. Rent was around 70% of my paycheck, so I did some math and estimated 3 years of this would give me enough cash to get my own place. Because of this our couple-weekends would probably be me going to visit him at his house (he would never go to my house because I have a car and can move to his place, yet my place is too far away for him).  At first I thought that the following series of events would just be a phase: getting there, seeing everything in a terrible mess, cleaning the floors, cleaning dishes, cooking dinner, buying groceries, taking dogs out for walk (while he played with a computer all weekend, since weekends are his resting time). Going out was crossed out after a while, since I got pissed off at paying for absolutely everything, and still doing what he wanted.
    I slowly discovered (unfortunately this is slowly because he is, regarding everything I have said above, as a person, a kind and good hearted man) that I was turning into a sex-benefit mother figure after him.  Even though things are not all black and white, and I have been using the “it is gray” excuse; there are clear boundaries which should not be crossed in my opinion. I tolerated not getting a single birthday or Valentine’s Day present because “he did not consider presents important”.
    It took me too long to find the answer, but losing one’s own identity is not negotiable in a relationship, no matter how much one can divide the aspects of life.  Even though you can talk about your sports with your running team buddies, or have the intellectual conversations with your university class mates, I got to a point where the monotonous (and in this case leeching-off-me) relationship was not worth it, I found myself preferring to be at work rather than with my couple, signing up for overtime and a stronger work load. Conversations with him would be plainly boring and repetitive, we had no activities in common, all we had in common was sex (and it got to a point where even that drifted apart).
    Why did I put up with it for so long? I thought that finding a good and kind (even wonderful in some aspects) person, who would put up with my tight schedule was hard enough to find. But this made me miserable.
    There are gray areas. But one’s own happiness comes first, if you pospone your goals and things you like to keep hold of a man that is not making the best out of most of the time together;  the relationship is not worth your while, as plain as black and white.

  12. 132

    Hi. CJ, Sadly, u & ur bf are not made for each other; what u r doing is just passing ur time until u find someone who is more of ur type ! Plz don’t take undue advantage of a guy’s love for u! Tell him how u feel; and plz be honest with yourself as well as with him. Seriously, 10 yrs of relationship & u still feel dissatisfied ! Break up girl !

  13. 133

    Wow, I am so impressed by the answer to this question! I’ve been having a similar issue and this was exactly the advice I needed. Great post.

  14. 134

    Fantastic response; with a face full of tears, I now know for certain MY kind and compatible guy is worth more to me than any intellectual.

  15. 135

    Wow… that was one heck of a great answer. I feel for CJ, and I see both sides. It’s a tough position to be in, and, I feel, a very modern position.

  16. 136

    Vino, I love your posts. I enjoy how you express yourself in a mature manner. Believe it or not, many men share your views. It is very depressing at times for men like us because the odds are drastically stacked against our favor, due to our genuine egalitarian stance on dating/marriage. I too use the same financial standards that the average woman expects from men, which is to only date those who either meet or exceed my level of income. As you have probably guessed, I have had no luck finding someone. Still, I will maintain my financial requirements of women in hopes that I will inspire more men to do the same. I won’t hold my breath, though.

    1. 136.1

       Lol mark trust me you won’t be holding your breath for too long. There are a lot of amazing wome  out there that work hard and can hold their own financially. Waiting for guys like you to come along . lol

  17. 137

    Evan, this was INCREDIBLE to read. Bravo. Very very touching, humbling, genuine. Evan, please keep writing. Wishing you the best of luck in everything!

  18. 138

    lol,VINO and Mark, poor u, two of you will be single for a very long time and end up in the nursery home…ALONE

  19. 139

    “I thought that finding a good and kind (even wonderful in some aspects) person, who would put up with my tight schedule was hard enough to find. But this made me miserable.
    There are gray areas. But one’s own happiness comes first, if you pospone your goals and things you like to keep hold of a man that is not making the best out of most of the time together;  the relationship is not worth your while, as plain as black and white.” — Love this, Caro Ferrero. I totally agree with you. Sometimes it just takes a long time before people realize that they are miserable.

  20. 140

    That was the best reply to a question like that I have ever seen. Bravo!

  21. 141

    i feel the exact same way towards my man we are 20 and 21   he just doesnt have drive.

  22. 142

    That compartmentalizing thing is not as easy as it appears even if women *should* be better able to do so.  I believe there is a book out with the title “Men Are Like Waffles, Women Are Like Spaghetti” with regard to that very subject.  And sometimes the reverse comes back to bite the more accomplished, ambitious partner in the relationship in the rear end.  I was in a relationship with someone who was not the “earner” that I am, who did not have the education, resume, etc.  It did not matter to me for the very reason that I did feel loved unconditionally.  However, I think it ultimately bothered him and caused him to decided one day just to never speak to me again after being in a 5 month relationship.  I didn’t judge him but he did me because if we did something, it was usually up to me to pay.  I didn’t see that as a permanent situation and was happy to do so just for the sake of being together but it was evidently not mutual.  Before we delve off into the woman being too masculine by doing that discussion, yes, I get that.  I guess at the end of the day, he’d rather have someone who needs to be rescued.  Of course I can only speculate.  He never communicated to me what was wrong, just decided to kick me to the curb.  Oh well, what are ya gonna do, right?

  23. 143

    …some men are accused of not communicating, sometimes by hi-powered women that, won’t listen in the first place….and why should they??..these women have the worlds attention….

  24. 144

    Except I’m not a high-powered anything.  I was mindful to always be respectful of him and not try to out-man him.  But I guess I’m just too flawed yet again.

  25. 145

    This reply is incredibly wise and smart. I am impressed  by the values that come across this article and the 2 questions asked are very intelligent. Great answer to a difficult question.
    I love how you make it clear that we can’t just expect to find a perfect person, we must complete certain needs ourselves or in other ways. To have someone who loves us, that we can just be with without talking and feeling happiness just by their presence, have good communication and common values, THAT is what matters. I was with a man who came from a prestigious family and although it made me feel secure socially, emotionally I was deprived and extremely stressed with him. Now I am going to marry someone, whom I wish was more driven and ambitious, but at the same time, makes me relax and enjoy life more, he actually made me realize that I am a woman, not just my job.

  26. 146
    Paul M

    “I will introduce your boyfriend to about a dozen of my single friends who are sick of game players and men who vanish and aren’t stable or steady,”
    Oh riiiight. It’s all the menz fault! It’s not the fault of – for instance – women who prefer to give it up for game players, losers, and flakes.
    The OP’s b/f would bore your friends just as hard as he bores her, and your friends would be complaining in almost the same words within a week or two. Every one of them has spent a lifetime rejecting a boatload of quality guys just like this one, and thoroughly deserves the future bearing down upon her.

  27. 147

    I agree with Paul M.
    Also, realize that while marriage may be a good deal for men on average, that might still not be a good deal for a man who is risk averse.  Suppose marriage involves a 60% chance of having typical benefits (live a few years longer, make 25% more money, have sex once more per week, and my wife enjoys it alot more – which does matter to men).  And a 25% chance of ending fairly soon and not much helping hindering my life (bad choice we both get over quickly).  And a 15% chance that I stay married 10+ years and then divorce, giving her half my accumulated wealth and plus ongoing alimony.  Some people might think a 50% chance of substantial benefit is worth taking a 15% chance of disaster.  But other people are going to choose to avoid a 15% chance of disaster pretty much no matter the odds of having a good outcome.
    And this is not really a “gender wars” issue.  Women face the same calculus.  Dcent chance of significantly good outcome but small chance of being SAHM for 20 years and then he dumps you for a younger model and skips town, hides his assets, and you are financially ruined.  And yet many women choose to get married and stay home with the kids.  Even though more and more don’t stay home. Many because they can’t afford to. Others because they can’t get comfortable taking such a huge risk.
    Life does not happen “on average”.  It happens in discrete outcomes.  It is a testament to the human spirit how many people get married despite knowing the existence of potential negative outcomes.  Hey, that is why divorced people go back into the dating pool!

  28. 148

    Absolutely amazing, Evan. I’ve been dealing with the same issue for a log time. Thank you for putting things into perspective. 

  29. 149

    As long as he’s working, I’d be okay with this.
    What’s not okay is the guy who spends his day watching television, while the woman goes out to work (unless, of course, he’s ill, child minding, or anything humane).

  30. 150

    although, they know little about relationships…………herds of single, coat/tie wearing, professional men do exist………….

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